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18 Things to Do in Boston This Week · June 25–28, 2026

Top Picks This Week

Lyle Lovett at City Winery

Americana legend Lyle Lovett performs multiple intimate nights at City Winery Boston — the perfect dinner-and-show date night.

Summer Concert Series & Beer Garden at Jason Russell House

Outdoor summer concert series and beer garden at the historic Jason Russell House in Arlington — a beloved seasonal tradition.

One Love 5K Family Fitness Challenge

Free 5K family fitness run and challenge event at the Melnea A. Cass Recreational Complex.

Festivals & Special Events
Fenway FC: Boston's Official Team USA Watch Party
Time Out Market Boston and Truly Hard Seltzer host a Team USA vs. Turkey watch party with food, drinks, games, and live entertainment.
Thursday, June 25, 2026 · Time Out Market Boston
Boston CentralCalShare
Summer Concert Series & Beer Garden at Jason Russell House
Outdoor summer concert series and beer garden at the historic Jason Russell House in Arlington — a beloved seasonal tradition.
Saturday, June 27, 2026 2:00 PM · Jason Russell House, Arlington
JoyraftCalShare
SoWa Open Market
Artisans, craftspeople, designers, and local farmers gather every Sunday in the South End's creative district for Boston's beloved outdoor market.
Sunday, June 28, 2026 11:00 AM · SoWa Boston, 530 Harrison Ave, South End
SoWa BostonCalShare
Arts & Culture
Lessons for a King (Boston)
The Silentwoods Collective performs baroque music by Rameau, Rebel, and others — works that covertly cautioned French monarchs against hubris — at Emmanuel Church's Lindsay Chapel.
Thursday, June 25, 2026 7:30 PM · Emmanuel Church, Lindsay Chapel, Boston
Boston Musical IntelligencerCalShare
In Old Age
Continuing theatrical run of this play at a Downtown Boston venue, with performances Thursday and beyond.
Thursday, June 25, 2026 7:30 PM · Downtown Boston
Downtown Boston AllianceCalShare
Bad Optics Opening at Anderson Yezerski
Opening of a new exhibition at Anderson Yezerski gallery in the South End — opening day June 26.
Friday, June 26, 2026 · Anderson Yezerski, South End, Boston
Boston Art RadarCalShare
Boston Art Book Fair Returns
The Boston Art Book Fair returns for another year — the city's premier gathering for zines, art books, small press, and independent publishers.
Saturday, June 27, 2026 · Boston
Boston Art ReviewCalShare
Free Events
Free Zumba on the Seaport Common
Free outdoor Zumba fitness class every Thursday through September — no experience needed, just sneakers and a water bottle.
Thursday, June 25, 2026 5:30 PM · Seaport Common, Northern Avenue, Boston
SweatpalsCalShare
City of Cambridge Dance Party
Thousands of Cambridge residents and visitors gather in front of Cambridge City Hall for this annual outdoor dance extravaganza.
Friday, June 26, 2026 · Cambridge City Hall, Cambridge
Boston CentralCalShare
Boston Harbor Hotel Summer in the City – Live Music
Free outdoor live music on the Harborwalk at the Boston Harbor Hotel, part of the Summer in the City 2026 series.
Friday, June 26, 2026 6:00 PM · Boston Harbor Hotel, Downtown Boston
Boston ShowsCalShare
Food & Drink
Summer Luau at Winthrop Center Park Beer Garden
A summer luau-themed outdoor beer garden pop-up at Winthrop Center Park in the heart of downtown.
Thursday, June 25, 2026 4:00 PM · Winthrop Center Park, Downtown Boston
Downtown Boston AllianceCalShare
Family-Friendly
Movie Night Under the Stars: Cool Runnings
Free outdoor film screening of the classic 'Cool Runnings' (PG) celebrating Caribbean American Heritage Month — connect with neighbors under the stars.
Friday, June 26, 2026 · Boston
Boston CentralCalShare
Music & Nightlife
Fish Tank Comedy
Stand-up comedy showcase at the intimate Rooted Armory Cafe in Somerville.
Friday, June 26, 2026 7:00 PM · Rooted Armory Cafe, Somerville
EventbriteCalShare
Chelsea Handler at Cape Cod Melody Tent
The uber-popular comedian, actress, and bestselling author returns to the Cape for a night of sharp, unfiltered humor.
Saturday, June 27, 2026 · Cape Cod Melody Tent
Boston TheaterCalShare
Sports
One Love 5K Family Fitness Challenge
Free 5K family fitness run and challenge event at the Melnea A. Cass Recreational Complex.
Saturday, June 27, 2026 9:00 AM · Melnea A. Cass Recreational Complex, Boston
Allevents.inCalShare
Outdoors & Active
Beyond Yoga x Pure Barre Pop-Up: Sculpt, Sweat + Shop
A free fitness pop-up combining a Pure Barre sculpt workout with a Beyond Yoga shopping experience.
Sunday, June 28, 2026 9:00 AM · Beyond Yoga, Boston
Allevents.inCalShare
Date Night
Lyle Lovett at City Winery
Americana legend Lyle Lovett performs multiple intimate nights at City Winery Boston — the perfect dinner-and-show date night.
Monday, June 29, 2026 · City Winery, 80 Beverly Street, Boston
City Winery BostonCalShare
'Paranormal Activity' Screening and Conversation
A special screening of 'Paranormal Activity' followed by an insider conversation at WBUR CitySpace — the perfect spooky summer date night.
Wednesday, July 8, 2026 · WBUR CitySpace, Boston
WBUR Events – CitySpaceCalShare